Waylon Jennings was the original country outlaw. Yes, Johnny had his troubles and Willie still does, but it was Waylon who invented the outlaw in country, and in so doing changed the music forever. His destiny perhaps was foretold when he notoriously cheated death early in his career: working as Buddy Holly's bass player, he gave up his plane seat at the last minute to rockabilly star J.P. Richardson, "The Big Bopper," on that fateful night “the music died.” The plane, which also carried Holly and 17-year-old Ritchie Valens, crashed, killing all aboard in February 1959. Jennings went on to become the archetypal country rebel, outraging many of the GOP, but ultimately fundamentally revitalizing dormant country airwaves with songs like “Good Hearted Woman” and “Mama Don’t Let Your Babies Grow Up to be Cowboys,” before finally succumbing to a diabetes-related illness in 2002.

There have been many Jennings greatest hits compilations over the years, but Waylon Jennings: Nashville Rebel, a four-disc box set that contains 92 songs in chronological order, encompasses nearly five decades of Jennings’ career, from his earliest Texas recordings produced by Buddy Holly in 1958, through to the final Highwayman album with Willie, Johnny and Kris Kristofferson in 1995, making it is his first truly comprehensive, career-spanning anthology.

It’s a dizzying collection that incorporates two decades of all the RCA
Victor recordings, including 16 No.1 singles, as well as signature
duets with wife Jessi Colter, Willie, Johnny and Hank Williams Jr. To
name just a few of Waylon’s most familiar: “Honky Tonk Heroes,” “Only
Daddy That’ll Walk the Line,” “Love of the Common People,” “Luckenbach,
Texas” (with Willie), “We Had It All,” “There Ain’t No Good Chain Gang”
(with Johnny Cash) and “Ladies Love Outlaws.”

The hits are familiar, endearing and ingrained, but the immediate
impression one gets from listening to this collection is just how much
musical territory Jennings covered stylistically. From Gordon
Lightfoot's "(That's What You Get) For Lovin' Me" and his bluesy take
of Little Richard's "Lucille," through classic and contemporary covers
like Jimmy Webb’s "MacArthur Park," Neil Young’s "Are You Ready for the
Country" and the Los Lobos standout "Will the Wolf Survive?," Waylon
really understood the heart and soul of true country music, from those
who came before him to those who have come after.

There’s a previously unreleased duet with Johnny Cash: "The Greatest
Cowboy of Them All" was recorded with the Tennessee Three and the
Carter Sisters in 1978, the same year that "Mamas Don't Let Your Babies
Grow Up to Be Cowboys," his duet with Nelson, spent four weeks at No. 1
on the country chart. And while the hits focus on the ‘70s and early
'80s, Jennings's commercial and creative heyday, the highlights here
extend from his early take on the Cajun classic "Jolie Blon," produced
by Jennings mentor Buddy Holly, through to the latter day recordings
with his Highwaymen pals.

Beyond other hits like "Are You Sure Hank Done It This Way,” "I Ain't
Living Long Like This," "Highwayman" and "Rose in Paradise," the
collection includes two tracks from 1969 that have never been released
in the U.S.: "It's Sure Been Fun" and "People in Dallas Got Hair."

Sound
The trademark lope of Jennings' music and his penchant for
self-mythologizing material gave him a strong signature sound that
always cut through in the studio, even in the early years when he
railed against the constraints of the Nashville studio system. There
was never mistaking a Waylon vocal. And, certainly during his prime
years when he had the confidence and the clout to rock out when he
wanted, the songs hold up with a resonance and vitality that not all
country classics maintain.

Extra Features
Nashville Rebel was put together by Jennings' widow Jessi Colter and
their son Shooter Jennings, and there is a sizable gallery of photos of
Waylon with friends, fellow musicians and every famous person he ever
met, from Muhammad Ali to Metallica's James Hetfield. The 140-page
booklet provides thorough credits and annotation, as well as extensive
essays by Jennings biographer (and Patti Smith guitarist) Lenny Kaye
and country historian Rich Kienzle.